DE60013803T2 - Tetracyclische azepinoindol verbindungen als 5-ht rezeptor liganden - Google Patents

Tetracyclische azepinoindol verbindungen als 5-ht rezeptor liganden Download PDF

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Publication number: DE60013803T2
Authority: DE; Germany
Prior art keywords: azepino; hexahydro; pyrrolo; quinoline; alkyl
Prior art date: 1999-04-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE60013803T

Other languages

German (de)

English (en)

Other versions

DE60013803D1 (de

Inventor

B. Jackson HESTER

N. Bruce ROGERS

Jon E. Jacobsen

Dalton Michael ENNIS

A. Brad ACKER

L. Susan VANDER VELDE

E. Kristine FRANK

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Pharmacia and Upjohn Co

Upjohn Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-23

Filing date

2000-04-20

Publication date

2005-11-17

2000-04-20 Application filed by Pharmacia and Upjohn Co, Upjohn Co filed Critical Pharmacia and Upjohn Co

2004-10-21 Application granted granted Critical

2004-10-21 Publication of DE60013803D1 publication Critical patent/DE60013803D1/de

2005-11-17 Publication of DE60013803T2 publication Critical patent/DE60013803T2/de

2020-04-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title description 8
ISZIQZCZKOFSBT-UHFFFAOYSA-N pyrrolo[2,3-g][1]benzazepine Chemical class N1=CC=CC=C2C3=NC=CC3=CC=C21 ISZIQZCZKOFSBT-UHFFFAOYSA-N 0.000 title description 8
102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 title description 6
239000003446 ligand Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 225
125000003118 aryl group Chemical group 0.000 claims description 159
125000000217 alkyl group Chemical group 0.000 claims description 144
125000001072 heteroaryl group Chemical group 0.000 claims description 107
238000002360 preparation method Methods 0.000 claims description 81
238000000034 method Methods 0.000 claims description 74
-1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 68
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 51
208000035475 disorder Diseases 0.000 claims description 40
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
150000002431 hydrogen Chemical class 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
125000001589 carboacyl group Chemical group 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
208000019901 Anxiety disease Diseases 0.000 claims description 15
125000004423 acyloxy group Chemical group 0.000 claims description 15
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
208000008589 Obesity Diseases 0.000 claims description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
235000020824 obesity Nutrition 0.000 claims description 13
208000011580 syndromic disease Diseases 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
125000005505 thiomorpholino group Chemical group 0.000 claims description 12
230000036506 anxiety Effects 0.000 claims description 11
125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
208000028017 Psychotic disease Diseases 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
210000003169 central nervous system Anatomy 0.000 claims description 10
125000004104 aryloxy group Chemical group 0.000 claims description 9
125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
101150065749 Churc1 gene Proteins 0.000 claims description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 8
102100038239 Protein Churchill Human genes 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
201000000980 schizophrenia Diseases 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
210000005095 gastrointestinal system Anatomy 0.000 claims description 7
208000019906 panic disease Diseases 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
208000019899 phobic disease Diseases 0.000 claims description 7
125000000464 thioxo group Chemical group S=* 0.000 claims description 7
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
206010034912 Phobia Diseases 0.000 claims description 6
201000001880 Sexual dysfunction Diseases 0.000 claims description 6
208000012826 adjustment disease Diseases 0.000 claims description 6
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
AJUJXTFALCYTJN-UHFFFAOYSA-N benzyl 14-methyl-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9(17),10,12-tetraene-5-carboxylate Chemical compound C1CC=2C(C3=4)=CC=CC=4C(C)CCN3C=2CCN1C(=O)OCC1=CC=CC=C1 AJUJXTFALCYTJN-UHFFFAOYSA-N 0.000 claims description 6
VDMQPQRFBKCCCS-UHFFFAOYSA-N benzyl 15-methyl-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene-5-carboxylate Chemical compound C1CC=2N(C3=4)CC(C)CC3=CC=CC=4C=2CCN1C(=O)OCC1=CC=CC=C1 VDMQPQRFBKCCCS-UHFFFAOYSA-N 0.000 claims description 6
NMGVPEQCGZWPFH-UHFFFAOYSA-N benzyl 16-methyl-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene-5-carboxylate Chemical compound C1CC=2N(C3=4)C(C)CCC3=CC=CC=4C=2CCN1C(=O)OCC1=CC=CC=C1 NMGVPEQCGZWPFH-UHFFFAOYSA-N 0.000 claims description 6
210000000748 cardiovascular system Anatomy 0.000 claims description 6
230000002496 gastric effect Effects 0.000 claims description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
231100000872 sexual dysfunction Toxicity 0.000 claims description 6
HNOXTRWCRXOABB-UHFFFAOYSA-N 10-benzoyl-5,6,8,9,10,11,12,12a-octahydro-4h,7ah-azepino[4',5':4,5]pyrrolo [3,2,1-ij]quinolin-4-ol Chemical compound C1CC2C(C3=4)=CC=CC=4C(O)CCN3C2CCN1C(=O)C1=CC=CC=C1 HNOXTRWCRXOABB-UHFFFAOYSA-N 0.000 claims description 5
OENLAVKOBUBYSP-UHFFFAOYSA-N 9-thia-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene Chemical compound C1=CSC2=CC=CC3=C2N1C=C3 OENLAVKOBUBYSP-UHFFFAOYSA-N 0.000 claims description 5
KXOIZANQDDKNDM-UHFFFAOYSA-N C1CNCCC2=C1C1=C3N2C(C)CCC3=CC=C1 Chemical compound C1CNCCC2=C1C1=C3N2C(C)CCC3=CC=C1 KXOIZANQDDKNDM-UHFFFAOYSA-N 0.000 claims description 5
BEINVFDIICWGLR-UHFFFAOYSA-N C1CNCCC2=C1C1=C3N2CC(C)CC3=CC=C1 Chemical compound C1CNCCC2=C1C1=C3N2CC(C)CC3=CC=C1 BEINVFDIICWGLR-UHFFFAOYSA-N 0.000 claims description 5
INYVOUYFBKUVQU-UHFFFAOYSA-N C1CNCCC2=C1N1CCC(C)C3=C1C2=CC=C3 Chemical compound C1CNCCC2=C1N1CCC(C)C3=C1C2=CC=C3 INYVOUYFBKUVQU-UHFFFAOYSA-N 0.000 claims description 5
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
HPLHOBPIYGRJMR-UHFFFAOYSA-N 10-benzoyl-4-methoxy-5,6,8,9,10,11,12,12a-octahydro-4h,7ah-azepino[4',5':4,5]pyrrolo[3,2,1-ij ]quinoline Chemical compound C1CC2C(C3=4)=CC=CC=4C(OC)CCN3C2CCN1C(=O)C1=CC=CC=C1 HPLHOBPIYGRJMR-UHFFFAOYSA-N 0.000 claims description 4
LZOQAYFBOAOQJQ-UHFFFAOYSA-N 10-benzoyl-5,6,9,10,11,12-hexahydro-4h,8h-azepino [4',5':4,5]pyrrolo[3,2,1-ij]quinolin-4-one Chemical compound C1CC(N2CCC(=O)C=3C=CC=C4C2=3)=C4CCN1C(=O)C1=CC=CC=C1 LZOQAYFBOAOQJQ-UHFFFAOYSA-N 0.000 claims description 4
JLTRNSWADPSQBA-UHFFFAOYSA-N 4-azatricyclo[5.3.1.04,11]undeca-1(11),2,5,7,9-pentaene Chemical compound C1=CC2=CC=CC3=C2N1C=C3 JLTRNSWADPSQBA-UHFFFAOYSA-N 0.000 claims description 4
206010001497 Agitation Diseases 0.000 claims description 4
206010003805 Autism Diseases 0.000 claims description 4
208000020706 Autistic disease Diseases 0.000 claims description 4
208000020925 Bipolar disease Diseases 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 4
208000019695 Migraine disease Diseases 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
206010047700 Vomiting Diseases 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
238000013019 agitation Methods 0.000 claims description 4
230000003542 behavioural effect Effects 0.000 claims description 4
DFAZLLSRRDGYNI-UHFFFAOYSA-N benzyl 1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene-5-carboxylate Chemical compound C1CC(N2CCCC=3C=CC=C4C2=3)=C4CCN1C(=O)OCC1=CC=CC=C1 DFAZLLSRRDGYNI-UHFFFAOYSA-N 0.000 claims description 4
238000002512 chemotherapy Methods 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
206010027599 migraine Diseases 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
230000008673 vomiting Effects 0.000 claims description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
VTUGFEKZLGZWIW-UHFFFAOYSA-N 1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene-15-thione Chemical compound C1CNCCC2=C1C1=C3N2CC(=S)CC3=CC=C1 VTUGFEKZLGZWIW-UHFFFAOYSA-N 0.000 claims description 3
GRFUDMGURJSJSC-UHFFFAOYSA-N 10,11-dibromo-14-oxa-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9(17),10,12-tetraene Chemical compound C1CNCCC2=C1N1CCOC3=C1C2=C(Br)C(Br)=C3 GRFUDMGURJSJSC-UHFFFAOYSA-N 0.000 claims description 3
CJLLIEJTESUJMN-UHFFFAOYSA-N 10,12-dibromo-14-oxa-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9(17),10,12-tetraene Chemical compound C1CNCCC2=C1C1=C(Br)C=C(Br)C3=C1N2CCO3 CJLLIEJTESUJMN-UHFFFAOYSA-N 0.000 claims description 3
MNZDIEHSPXNVIE-UHFFFAOYSA-N 10-(2-naphthalen-1-yloxyethoxy)-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1CNCCC(C2=C34)=C1N4CCCC3=CC=C2OCCOC1=CC=CC2=CC=CC=C12 MNZDIEHSPXNVIE-UHFFFAOYSA-N 0.000 claims description 3
YZVZSBDBFWUQSI-UHFFFAOYSA-N 10-(2-naphthalen-2-yloxyethoxy)-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1CNCCC(C2=C34)=C1N4CCCC3=CC=C2OCCOC1=CC=C(C=CC=C2)C2=C1 YZVZSBDBFWUQSI-UHFFFAOYSA-N 0.000 claims description 3
JFPHPIOXETYUOL-UHFFFAOYSA-N 10-[2-(2-bromophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound BrC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 JFPHPIOXETYUOL-UHFFFAOYSA-N 0.000 claims description 3
QFLXDXXZQDDRDZ-UHFFFAOYSA-N 10-[2-(2-chlorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound ClC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 QFLXDXXZQDDRDZ-UHFFFAOYSA-N 0.000 claims description 3
AYFZQWALBMKRTI-UHFFFAOYSA-N 10-[2-(2-fluorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound FC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 AYFZQWALBMKRTI-UHFFFAOYSA-N 0.000 claims description 3
DQQOXDPTMCOVGY-UHFFFAOYSA-N 10-[2-(2-methoxyphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound COC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 DQQOXDPTMCOVGY-UHFFFAOYSA-N 0.000 claims description 3
UMKNVFQIWUKCHM-UHFFFAOYSA-N 10-[2-(2-methylphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound CC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 UMKNVFQIWUKCHM-UHFFFAOYSA-N 0.000 claims description 3
RWXZGHNYBLLFRP-UHFFFAOYSA-N 10-[2-(2-phenylphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C=1C=C(C=23)CCCN3C=3CCNCCC=3C=2C=1OCCOC1=CC=CC=C1C1=CC=CC=C1 RWXZGHNYBLLFRP-UHFFFAOYSA-N 0.000 claims description 3
JDSRBDHWLVMFGJ-UHFFFAOYSA-N 10-[2-(3-bromophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound BrC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 JDSRBDHWLVMFGJ-UHFFFAOYSA-N 0.000 claims description 3
ZWZXPJJEQIOCPG-UHFFFAOYSA-N 10-[2-(3-chlorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound ClC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 ZWZXPJJEQIOCPG-UHFFFAOYSA-N 0.000 claims description 3
RTROOVGFLSHJAC-UHFFFAOYSA-N 10-[2-(3-fluorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound FC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 RTROOVGFLSHJAC-UHFFFAOYSA-N 0.000 claims description 3
KBKACWUAKUJJLX-UHFFFAOYSA-N 10-[2-(3-methoxyphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound COC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 KBKACWUAKUJJLX-UHFFFAOYSA-N 0.000 claims description 3
UCRCJZDBZUDISW-UHFFFAOYSA-N 10-[2-(3-methylphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound CC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 UCRCJZDBZUDISW-UHFFFAOYSA-N 0.000 claims description 3
VEWWYDZHKHQJFR-UHFFFAOYSA-N 10-[2-(4-bromophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(Br)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 VEWWYDZHKHQJFR-UHFFFAOYSA-N 0.000 claims description 3
QQTPHXVOBMYGQJ-UHFFFAOYSA-N 10-[2-(4-chlorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(Cl)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 QQTPHXVOBMYGQJ-UHFFFAOYSA-N 0.000 claims description 3
RADXMOBTYGSHDI-UHFFFAOYSA-N 10-[2-(4-fluorophenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(F)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 RADXMOBTYGSHDI-UHFFFAOYSA-N 0.000 claims description 3
MPMRDVMFRFQDIX-UHFFFAOYSA-N 10-[2-(4-methoxyphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(OC)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 MPMRDVMFRFQDIX-UHFFFAOYSA-N 0.000 claims description 3
GWMKVEISSFBMPP-UHFFFAOYSA-N 10-[2-(4-methylphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(C)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 GWMKVEISSFBMPP-UHFFFAOYSA-N 0.000 claims description 3
DSTXTPRXMMOVJL-UHFFFAOYSA-N 10-[2-(4-phenylphenoxy)ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C=1C=C(C=23)CCCN3C=3CCNCCC=3C=2C=1OCCOC(C=C1)=CC=C1C1=CC=CC=C1 DSTXTPRXMMOVJL-UHFFFAOYSA-N 0.000 claims description 3
NDGITKUTJXOLDP-UHFFFAOYSA-N 10-[2-[2-(trifluoromethoxy)phenoxy]ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound FC(F)(F)OC1=CC=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 NDGITKUTJXOLDP-UHFFFAOYSA-N 0.000 claims description 3
UIZBTYNVLXLSQT-UHFFFAOYSA-N 10-[2-[3-(trifluoromethoxy)phenoxy]ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound FC(F)(F)OC1=CC=CC(OCCOC=2C=3C=4CCNCCC=4N4CCCC(C=34)=CC=2)=C1 UIZBTYNVLXLSQT-UHFFFAOYSA-N 0.000 claims description 3
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HDEYKCRTVLSXBX-UHFFFAOYSA-N 10-[2-[4-(trifluoromethoxy)phenoxy]ethoxy]-1,5-diazatetracyclo[7.7.1.02,8.013,17]heptadeca-2(8),9,11,13(17)-tetraene Chemical compound C1=CC(OC(F)(F)F)=CC=C1OCCOC1=CC=C2C3=C1C(CCNCC1)=C1N3CCC2 HDEYKCRTVLSXBX-UHFFFAOYSA-N 0.000 claims description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
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DE60013803T 1999-04-23 2000-04-20 Tetracyclische azepinoindol verbindungen als 5-ht rezeptor liganden Expired - Fee Related DE60013803T2 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US13081199P	1999-04-23	1999-04-23
US130811P		1999-04-23
PCT/US2000/010600 WO2000064899A1 (en)	1999-04-23	2000-04-20	Tetracyclic azepinoindole compounds as 5-ht receptor ligands

Publications (2)

Publication Number	Publication Date
DE60013803D1 DE60013803D1 (de)	2004-10-21
DE60013803T2 true DE60013803T2 (de)	2005-11-17

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Application Number	Title	Priority Date	Filing Date
DE60013803T Expired - Fee Related DE60013803T2 (de)	1999-04-23	2000-04-20	Tetracyclische azepinoindol verbindungen als 5-ht rezeptor liganden

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EP (1)	EP1173440B1 (es)
JP (1)	JP2002543080A (es)
KR (1)	KR20020005708A (es)
CN (1)	CN1183132C (es)
AR (1)	AR023574A1 (es)
AT (1)	ATE276255T1 (es)
AU (1)	AU760943C (es)
BR (1)	BR0009983A (es)
CA (1)	CA2367682A1 (es)
DE (1)	DE60013803T2 (es)
DK (1)	DK1173440T3 (es)
EC (1)	ECSP003426A (es)
ES (1)	ES2226822T3 (es)
HK (1)	HK1045512B (es)
NZ (1)	NZ514553A (es)
PE (1)	PE20010052A1 (es)
PT (1)	PT1173440E (es)
SI (1)	SI1173440T1 (es)
WO (1)	WO2000064899A1 (es)
ZA (1)	ZA200108636B (es)

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2000
- 2000-04-19 PE PE2000000368A patent/PE20010052A1/es not_active Application Discontinuation
- 2000-04-19 AR ARP000101881A patent/AR023574A1/es unknown
- 2000-04-20 ES ES00923532T patent/ES2226822T3/es not_active Expired - Lifetime
- 2000-04-20 NZ NZ514553A patent/NZ514553A/en unknown
- 2000-04-20 DE DE60013803T patent/DE60013803T2/de not_active Expired - Fee Related
- 2000-04-20 AU AU43637/00A patent/AU760943C/en not_active Ceased
- 2000-04-20 DK DK00923532T patent/DK1173440T3/da active
- 2000-04-20 HK HK02107016.3A patent/HK1045512B/zh not_active IP Right Cessation
- 2000-04-20 WO PCT/US2000/010600 patent/WO2000064899A1/en not_active Ceased
- 2000-04-20 EP EP00923532A patent/EP1173440B1/en not_active Expired - Lifetime
- 2000-04-20 BR BR0009983-0A patent/BR0009983A/pt not_active IP Right Cessation
- 2000-04-20 JP JP2000614251A patent/JP2002543080A/ja active Pending
- 2000-04-20 AT AT00923532T patent/ATE276255T1/de not_active IP Right Cessation
- 2000-04-20 SI SI200030516T patent/SI1173440T1/xx unknown
- 2000-04-20 PT PT00923532T patent/PT1173440E/pt unknown
- 2000-04-20 CN CNB008066639A patent/CN1183132C/zh not_active Expired - Fee Related
- 2000-04-20 KR KR1020017013458A patent/KR20020005708A/ko not_active Ceased
- 2000-04-20 CA CA002367682A patent/CA2367682A1/en not_active Abandoned
- 2000-04-27 EC EC2000003426A patent/ECSP003426A/es unknown
2001
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Publication number	Publication date
NZ514553A (en)	2003-10-31
SI1173440T1 (en)	2005-02-28
AU760943B2 (en)	2003-05-22
CN1348454A (zh)	2002-05-08
HK1045512B (zh)	2005-09-02
ATE276255T1 (de)	2004-10-15
AU760943C (en)	2003-12-04
DE60013803D1 (de)	2004-10-21
AU4363700A (en)	2000-11-10
ES2226822T3 (es)	2005-04-01
ZA200108636B (en)	2003-02-19
JP2002543080A (ja)	2002-12-17
WO2000064899A1 (en)	2000-11-02
EP1173440A1 (en)	2002-01-23
ECSP003426A (es)	2000-10-24
AR023574A1 (es)	2002-09-04
EP1173440B1 (en)	2004-09-15
CN1183132C (zh)	2005-01-05
HK1045512A1 (en)	2004-10-15
PT1173440E (pt)	2004-12-31
PE20010052A1 (es)	2001-01-27
BR0009983A (pt)	2002-04-16
DK1173440T3 (da)	2004-12-20
KR20020005708A (ko)	2002-01-17
CA2367682A1 (en)	2000-11-02

Publication	Publication Date	Title
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